I was a Gambling Man

I fucked up. Not just one fuck up, but a long string of fuck ups. I’m sitting in my apartment, drinking some cheap whiskey in my relatively bare apartment. Looking down at my bank app, the negative balance cut into my heart.

I’m Carl Carpenter, a 28 year old analyst for a distribution company. I made good money there, enough to support myself and shouldn’t have to worry about bills being paid and saving for the future with my girlfriend, Allison. But I’m also Carl Carpenter, the addictive gambler, and a bad one at that. Cut off from all the legal sports books and casinos for gambling too often outside of my means “for my own protection” they say, I resorted to sketchy off-shore gambling books. They didn’t care if you sold a kidney to pay them as long as they got paid. And I hadn’t paid.

I stared down at my phone sitting on the couch at the string of texts from my bookie, asking where the loan money was. Each one got less friendly and more curt and angry. I calmed him down and he gave me a month to pay him back, or else. But $50,000 was a lot of money, money i didn’t have and had no means to get it. Parents wouldn’t be any help. My sister was a barista so no help there. None of my friends had that much lying around.

And my girlfriend was a secretary at big corporation but she didn’t have nearly that much money in her savings. And if she knew how deep in debt I was, there’s no way she’d stay with him. She knew I liked to gamble but did not in any means like it. No, I can’t go to her for help, but what else was there?

I finished my cheap whiskey and filled another glass as I browsed the internet on my laptop. They whiskey was taking hold of me so I went to another cheap easy release, porn. Something to take my mind off all the stress in my life, at least in the short term. I pulled up my typical cam girl site and dozens of girls popped up in various states of undress in their thumbnail pictures. Some in tight little outfits, others in lingerie, and some showing dildos or cocks entering one or another or a combination of holes.

God, girls had it easy. All they had to do was look hot and money would just fall in their laps. But guys? No, we had to work for our money. Why was life so unfair? I thought this as I unzipped my pants to watch a hot brunette take off her shirt to show her bra cause some guys tipped her $100. She wasn’t even showing really anything, some girls would wear that as a top nowadays so what’s the harm in that. She didn’t even really do anything sexual. Easiest $100 of her life.

And that’s when it hit me. It was probably all the booze in my system, or the stress from the threat of my knee caps being shattered, or the horniness I was feeling at the moment. But, I thought I could do that. Throw on some lingerie and a dress? I’m not a big guy, only 5’6” and 150 lbs. I go to the gym, well really the stair master not a big weights guy just trying to stay trim. My body looks pretty lithe. Not a ton of body hair. And laptop cameras aren’t great you probably can’t even see it.

Before I knew it, I had downed another glass of whiskey to summon up the courage. Quick work with a razor cleaned up whatever sparse hair I had on my face, as well as my chest and pits, thinking no one wanted to see a hairy armpit on a girl. I left my arm hair alone, not willing to go that far. I kept my downstairs area trimmed up so left that alone. But a few hairs at the small of my back and on my cheeks were gone in a flash. I briefly considered shaving my legs but I was only planning on going torso up so left those alone.

Freshly smooth from the face to my thighs, I drunkenly walked into my bedroom naked. I went over to the dresser that had some of my girlfriend Allison’s clothes she’s left over the year or so we’d been dating. Steeling my nerves, I opened the drawer to a multitude of bright colors and light delicate fabrics of her lingerie. Typically, Allie wore conservative and comfortable bras and panties. She wasn’t a nun by any means but she was more practical with her day to day underwear than I would like. Calvin Klein soft cotton bras and panties and thongs. T shirt bras and the like. A few VS items but nothing too crazy. But her racy stuff, stuff I’ve bought for her as gifts, that are more so gifts for me to have her wear, as well as things she bought for date nights are left here. Well, I guess now they are more so for me than her as I lifted a lacy fire engine red thong that left little to the imagination with its small triangle of fabric in the front and just a thin string in the back.

I held it in front of me and seeing how small it was there’s no way my junk could fit. I wasn’t massive by any means, but my 6 inch cock would never fit in this tiny scrap of fabric. I put it back and rummaged through some more. I steered away from the girly pinks and bright neons and pastels as I couldn’t bring myself to put on something so girly. Ironic as I was looking for lingerie to wear. But then I saw a set that would work.

The panties were black mesh and velvet high waisted but cut high on the thighs. The velvet panel in front covered a triangle in front, preserving some modesty, where the back and sides were the sheer see through mesh, leaving the butt covered but seen. The bra was one of those corset tops, not a full blown corset like Victorian times, but one that he’d seen girls wear as tops. Maybe bustier? I had no idea but it was incredibly sexy. Two thin black straps went over the shoulders like a tank top, connecting to the black velvet push up bra cups. The bustier went down to just below his ribcage in the front in an inverted triangle with the same velvety soft black fabric. Similar to the panties, the sides and back were sheer black mesh showing his skin. 4 hooks in the back tightened the piece together.

Laying the lingerie set out, I remembered Allie wearing this set for him on a date night a few months ago. They’d had a few glasses of wine at dinner and when they got home she was feeling especially frisky and surprised him in the living room wearing it. He couldn’t keep his hands off her seeing how hot she looked and they fucked like rabbits all night long. The memory made me falter as I reached for the panties, could I really do this? Should I? But the drink in my system and the fear of broken legs made me shake it off as I shakily snaked the panties up my legs.

The mesh and velvet felt incredible on my skin, so much different than my cotton boxer briefs. It felt….. good. I felt my member start to stiffen, making an obscene bulge in the front. Quickly, I shoved my semi between my legs and hiked the panties up higher trapping it between. It was uncomfortable, especially on my balls as they were smushed with my cock splitting between them, but it made the front look much smoother but not perfect. Id need to find something to cover that up. How did those dudes on drag race do it? There had to be another way, but I’ll figure that out later.

The panties were one thing as I could kind of pretend they were mens briefs. But looking at the bustier, an article of clothing no guy would ever need as we didn’t have the “equipment” to make it necessary, I hesitated again. Should I really be doing this? This feels like I’m crossing the rubicon and there’s no going back. I could just forget about it and figure out another way to make that money back while holding onto my manhood. But, that fear of getting hurt and losing everything won out.

“Come on, Carl, man up and put on the fucking bra dude. It’s not gunna make you gay. It’s just clothes. You can do this” I said to myself trying to psyche me up.

Fiddling with the clasps on the bustier, I finally got it undone and wrapped it around my torso, the thin straps cutting into my shoulders. I struggled for a few minutes getting it clasped behind me finally getting it done with a breath of relief. While a little tight even on the widest setting, it fit well enough on my torso, even bringing in my waist a bit giving a slight feminine curve to my thin frame. For the first time ever I was happy that his girlfriend was smaller chested at only a B cup. Sure, I’d never had an issue with Allie’s chest, but what guy doesn’t want larger breasts on his girl? But now, the super push up padding and some manipulation of my chest fat made it look like I had B maybe even C cups, perky and tight with some generous cleavage in between.

Looking in the mirror, I ignored my face and looked at the body, surprisingly pleased while also embarrassed with how I looked. Just a pair of panties and a bustier and I looked pretty girly. I’d need to go to the gym to bulk up after all this is over. Sure, i wasn’t a bikini model, but just looking at his body it didn’t scream man in lingerie, but a slightly flat and not as curvy girl. But the slight bulge in front needed to be covered.

Rummaging around some more drawers I found something that would work perfectly, covering up my junk and also playing into the cam girl image. A black and red tartan high waisted school girl skirt with a lacy black trim on the hemline with a fitted white blouse. The skirt would never pass dress code at a school as it was obscenely short, but the pleated skirt would cover up his junk and flare out from his hips giving him some more curves. The black lace details on the hem added even more sexiness to the outfit. Sliding it up my legs felt good but weird, having never worn a skirt before. The air flow between my legs was odd but surprisingly welcome. The skirt came just a few inches below my butt, leaving my thighs out in the open. Seeing the hair on my legs coming out from under the skirt looked weird, kinda wishing I’d gone along with it and shaved them but too late for that now. Thankfully, the set came with a pair of opaque white thigh high socks with red and black tartan bows on the front and back. Sliding them up his legs trying to not rip them I settled them on my thighs, straightening the bows at the top. There was a thin sliver of skin showing between the socks and my skirt but thankfully the hair wasn’t noticeable.

Looking in the mirror from the neck down I saw a slutty school girl wearing an outfit for either Halloween or her boyfriend’s private birthday party in his bedroom. It weirded me out seeing my body like this, but also strangely pleased that I looked pretty good. The skirt twirled around as I moved my hips to look at my butt, like I’d seen Allison do a thousand times before going out, giving me a strange thrill seeing the skirt flare out and up giving a little peek of my pantied butt. The **** was definitely getting to me as I thought that was the funniest thing in the world.

“Man I look like a slut hahahaha” I drunkenly laughed to myself.

But my work wasn’t finished yet as my face and head needed some work. I had no idea what to do with make up at all, even if I had all the gunk girls put on themselves. But I did have Allie’s red lipstick and a lip liner pencil. If I just keep the camera at my lips and below, that should work. He’d seen plenty of cam girls and OF girls make bank and never show their face. So with a quick YouTube video, as the first attempt made me look like a clown who knew putting on lipstick took that many steps?, I was able to outline my lips a bit more than the natural line, making them look much larger. I laughed at myself making a kissy face at the mirror cause they looked pretty damn good! The thought of DSLs came to mind and I gagged a bit at the thought.

Finally, I grabbed the long brunette wig from another costume I’d gotten Allie. The brunette wig had two big pigtails that went past my shoulders in length with red bows at the base of each. Blunt bangs that went straight across the forehead with a little curl in them. Allie looked so fucking hot in it paired with the slutty cheerleader outfit. She enjoyed it a bit, even if she was shy and a little degraded by the slutty outfit. But she didn’t like how much i enjoyed it, as she felt like i was imagining her as a different girl so we never tried it again. Damn shame.

Slipping on the wig, I looked at myself in the mirror and was shocked. Besides my eyes, I looked pretty damn good! My thin body and arms looked fairly natural in this little school girl outfit. And my legs, while not a twerking model on insta’s legs, looked really good in the white stockings. My butt, maybe a little plump for a guy but nothing too crazy, looked much bigger due to the pleated skirt. And my chest looked surprisingly believable, well more like a flat chested girl doing everything in her power to get some size up top but the cleavage looked amazing. I involuntarily licked my big red lips while holding a hand up to my faux boobs. Seeing the girl in the mirror do the same an ache came from my tucked back little guy. I shook myself from staring, my pig tails whipping back and forth, before stepping away from the mirror.

Walking to the living room was a different experience. The skirt swaying back and forth on my hips and legs. The socks rubbing against each other electrically. The pig tails bouncing to and fro. It was completely alien to me and a little scary but strangely, and I blame the **** for this, a little erotic. I even put a little wiggle in my hips as I walked. But the reality of why I was dressed like this set in my brain, so I quickly poured myself an another drink of cheap whiskey, downing it quickly before pouring another. The **** settled my nerves relaxing me for the moment before I saw the red lipstick stain on my glass. I stared at it drunkenly thinking about how different it was to see it on my glass rather than another girls. Snapping out of my drunken thoughts, I was reminded of why I had a red lipstick stain in the first place and walked over to the couch.

Moving some packages out of my seat on the couch, I sat behind my laptop and pulled up a cam girl site. Quickly entering some details, I was stuck on what I should call myself. Can’t go by Carl dressed like this obviously. Carly immediately came to mind and it felt right, but it was too close to my real name. It needed to be much more stripper-y.

I remember a stripper at a buddy’s bachelor party who was smoking hot. Big fakies with bimbo platinum blonde hair. God she was hot, but I was so drunk I barely remember the night, except for my buddies laughing when the groom took her into the bed room of the hotel suite. Never found out why but two of them were laughing up a storm as he took her hand and she minced in with those big stripper heels. She didn’t have a male pimp either. Some big red headed woman who was gorgeous too. Scary chick, but hot as hell. She kept eyeing me up but she scared the hell out of me. The groom was one lucky son of a bitch what was her name? Candi! That’s it! If I’m gunna be a whore, might as well lean into it with the name, so Candi Cream was born as I typed it in.

“Submit?” Came up on screen and I hit it without thinking. Navigating through my profile I found the stream link and hesitated, my hand hovering over the button. Should I do this? Was it worth my masculinity? Glancing over at my phone and seeing more texts from my bookie was all it took. I steeled my resolve with a deep breath and clicked stream…